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CHEBI:65909 - forskoditerpenoside E

ChEBI IDCHEBI:65909
ChEBI Nameforskoditerpenoside E
Stars
DefinitionA diterpene glycoside that is labd-14-en-11-one substituted by β-acetoxy group at position 6, an epoxy group between positions 8 and 13 and a β-D-glucopyranosyloxy group at position 1 (the 1α stereoisomer). Isolated from the whole plant of Coleus forskohlii, it shows relaxative effects on isolated guinea pig tracheal spirals in vitro.
Last Modified25 January 2013
DownloadsMolfile
FormulaC28H44O10
Net Charge0
Average Mass540.650
Monoisotopic Mass540.29345
SMILES[H][C@@]1(O[C@H]2CCC(C)(C)[C@]3([H])[C@H](OC(C)=O)C[C@@]4(C)O[C@@](C)(C=C)CC(=O)[C@]4([H])[C@@]23C)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C28H44O10/c1-8-26(5)11-15(31)22-27(6,38-26)12-16(35-14(2)30)23-25(3,4)10-9-18(28(22,23)7)37-24-21(34)20(33)19(32)17(13-29)36-24/h8,16-24,29,32-34H,1,9-13H2,2-7H3/t16-,17-,18+,19-,20+,21-,22+,23+,24+,26+,27-,28-/m1/s1
InChIKeyZBNOVDLAFYUSJT-KHGPFLBYSA-N
Species of MetaboliteComponentSourceComments
Coleus forskohlii (ncbitaxon:41228) whole plant (BTO:0001461) PubMed (18175974)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
muscle relaxant  A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
ChEBI Ontology
Outgoing Relation(s)
forskoditerpenoside E (CHEBI:65909) has role metabolite (CHEBI:25212)
forskoditerpenoside E (CHEBI:65909) has role muscle relaxant (CHEBI:51371)
forskoditerpenoside E (CHEBI:65909) is a acetate ester (CHEBI:47622)
forskoditerpenoside E (CHEBI:65909) is a cyclic ether (CHEBI:37407)
forskoditerpenoside E (CHEBI:65909) is a cyclic ketone (CHEBI:3992)
forskoditerpenoside E (CHEBI:65909) is a diterpene glycoside (CHEBI:71939)
forskoditerpenoside E (CHEBI:65909) is a labdane diterpenoid (CHEBI:36770)
forskoditerpenoside E (CHEBI:65909) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
(3R,4aR,6R,6aS,10S,10aS,10bR)-10-(β-D-glucopyranosyloxy)-3,4a,7,7,10a-pentamethyl-1-oxo-3-vinyldodecahydro-1H-benzo[f]chromen-6-yl acetate
Synonym  Source
6β-acetoxy-8,13-epoxy-labd-14-en-11-one-1α-O-β-D-glucopyranosideChEBI
Registry NumbersSources
Reaxys:15762062Reaxys
Citations